Identification

Name
Memantine
Accession Number
DB01043  (APRD00221)
Type
Small Molecule
Groups
Approved, Investigational
Description

Memantine is an amantadine derivative with low to moderate-affinity for NMDA receptors. It is a noncompetitive NMDA receptor antagonist that binds preferentially to NMDA receptor-operated cation channels. It blocks the effects of excessive levels of glutamate that may lead to neuronal dysfunction. It is under investigation for the treatment of Alzheimer's disease, but there has been no clinical support for the prevention or slowing of disease progression.

Structure
Thumb
Synonyms
  • 1-Amino-3,5-dimethyladamantane
  • 1,3-Dimethyl-5-adamantanamine
  • 3,5-Dimethyl-1-adamantanamine
  • 3,5-Dimethyl-1-aminoadamantane
  • 3,5-Dimethyltricyclo(3.3.1.1(3,7))decan-1-amine
  • Memantina
  • Memantine
  • Memantinum
External IDs
D-145 / DRG-0267
Product Ingredients
IngredientUNIICASInChI Key
Memantine HydrochlorideJY0WD0UA6041100-52-1LDDHMLJTFXJGPI-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act MemantineTablet5 mgOralActavis Pharma CompanyNot applicableNot applicableCanada
Act MemantineTablet10 mgOralActavis Pharma Company2010-02-18Not applicableCanada
AxuraTablet, film coated20 mgOralMerz Pharmaceuticals2002-05-17Not applicableEu
AxuraTablet, film coated20 mgOralMerz Pharmaceuticals2002-05-17Not applicableEu
AxuraTablet, film coated10 mgOralMerz Pharmaceuticals2002-05-17Not applicableEu
AxuraTablet, film coated10 mgOralMerz Pharmaceuticals2002-05-17Not applicableEu
AxuraTablet, film coated20 mgOralMerz Pharmaceuticals2002-05-17Not applicableEu
AxuraTablet, film coated10 mgOralMerz Pharmaceuticals2002-05-17Not applicableEu
AxuraTablet, film coated10 mgOralMerz Pharmaceuticals2002-05-17Not applicableEu
AxuraTablet, film coated20 mgOralMerz Pharmaceuticals2002-05-17Not applicableEu
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-memantineTablet10 mgOralApotex Corporation2011-06-17Not applicableCanada
MarixinoTablet, film coated10 mgOralConsilient Health Ltd2013-04-29Not applicableEu
MarixinoTablet, film coated20 mgOralConsilient Health Ltd2013-04-29Not applicableEu
MarixinoTablet, film coated10 mgOralConsilient Health Ltd2013-04-29Not applicableEu
MarixinoTablet, film coated20 mgOralConsilient Health Ltd2013-04-29Not applicableEu
MarixinoTablet, film coated10 mgOralConsilient Health Ltd2013-04-29Not applicableEu
MarixinoTablet, film coated20 mgOralConsilient Health Ltd2013-04-29Not applicableEu
MarixinoTablet, film coated10 mgOralConsilient Health Ltd2013-04-29Not applicableEu
MarixinoTablet, film coated20 mgOralConsilient Health Ltd2013-04-29Not applicableEu
MarixinoTablet, film coated10 mgOralConsilient Health Ltd2013-04-29Not applicableEu
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Memantine HydrochlorideTablet, film coated5 mg/1OralCadila Pharnmaceuticals2017-09-28Not applicableUs
Memantine HydrochlorideTablet, film coated10 mg/1OralCadila Pharnmaceuticals2017-09-28Not applicableUs
International/Other Brands
Abixa / Akatinol / Axura / Memox
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Memantine and Donepezil Hydrochlorides Extended-releaseMemantine Hydrochloride (28 mg/1) + Donepezil hydrochloride (10 mg/1)Capsule, extended releaseOralAmneal Pharmaceuticals2017-02-01Not applicableUs
Memantine and Donepezil Hydrochlorides Extended-releaseMemantine Hydrochloride (14 mg/1) + Donepezil hydrochloride (10 mg/1)Capsule, extended releaseOralAmneal Pharmaceuticals2017-02-01Not applicableUs
NamzaricMemantine Hydrochloride (28 mg/1) + Donepezil hydrochloride (10 mg/1)CapsuleOralAllergan2014-12-24Not applicableUs
NamzaricMemantine Hydrochloride + Donepezil hydrochlorideKitOralAllergan2016-11-28Not applicableUs
NamzaricMemantine Hydrochloride (7 mg/1) + Donepezil hydrochloride (10 mg/1)CapsuleOralAllergan2016-07-18Not applicableUs
NamzaricMemantine Hydrochloride (14 mg/1) + Donepezil hydrochloride (10 mg/1)CapsuleOralAllergan2014-12-24Not applicableUs
NamzaricMemantine Hydrochloride (21 mg/1) + Donepezil hydrochloride (10 mg/1)CapsuleOralAllergan2016-07-18Not applicableUs
Categories
UNII
W8O17SJF3T
CAS number
19982-08-2
Weight
Average: 179.3018
Monoisotopic: 179.167399677
Chemical Formula
C12H21N
InChI Key
BUGYDGFZZOZRHP-UHFFFAOYSA-N
InChI
InChI=1S/C12H21N/c1-10-3-9-4-11(2,6-10)8-12(13,5-9)7-10/h9H,3-8,13H2,1-2H3
IUPAC Name
3,5-dimethyladamantan-1-amine
SMILES
CC12CC3CC(C)(C1)CC(N)(C3)C2

Pharmacology

Indication

For the treatment of moderate to severe dementia of the Alzheimer's type.

Structured Indications
Pharmacodynamics

Memantine, an amantadine derivative, is an NMDA receptor antagonist used in the treatment of Alzheimer's disease. It differs from traditional agents used in Alzheimer's disease by acting on glutamatergic neurotransmission, rather than cholinergic. There is some evidence that dysfunction of glutamatergic neurotransmission, manifested as neuronal excitotoxicity, is involved in the aetiology of Alzheimer's disease (Cacabelos et al., 1999). As such, targeting the glutamatergic system, specifically NMDA receptors, was a novel approach to treatment in view of the limited efficacy of existing drugs targeting the cholinergic system. A systematic review of randomised controlled trials found that memantine has a positive effect on cognition, mood, behaviour, and the ability to perform daily activities. There is no evidence that memantine prevents or slows neurodegeneration in patients with Alzheimer's disease.

Mechanism of action

Memantine exerts its action through uncompetitive NMDA receptor antagonism, binding preferentially to the NMDA receptor-operated cation channels. Prolonged increased levels of glutamate in the brain of demented patients are sufficient to counter the voltage-dependent block of NMDA receptors by Mg2+ ions and allow continuous influx of Ca2+ ions into cells, ultimately resulting in neuronal degeneration. Studies suggest that memantine binds more effectively than Mg2+ ions at the NMDA receptor, and thereby effectively blocks this prolonged influx of Ca2+ ions through the NMDA channel whilst preserving the transient physiological activation of the channels by higher concentrations of synaptically released glutamate. Thus memantine protects against chronically elevated concentrations of glutamate. Memantine also has antagonistic activity at the type 3 serotonergic (5-HT3) receptor with a potency that is similar to that at the NMDA receptor, and lower antagonistic activity at the nicotinic acetylcholine receptor. This drug has no affinity for γ-aminobutyric acid (GABA), benzodiazepine, dopamine, adrenergic, histamine, or glycine receptors or for voltage-dependent calcium, sodium, or potassium channels.

TargetActionsOrganism
AGlutamate receptor ionotropic, NMDA 3A
antagonist
Human
AGlutamate receptor ionotropic, NMDA 2A
antagonist
Human
AGlutamate receptor ionotropic, NMDA 2B
antagonist
Human
U5-hydroxytryptamine receptor 3A
antagonist
Human
UAlpha-7 nicotinic cholinergic receptor subunit
antagonist
Human
UD(2) dopamine receptor
agonist
Human
UGlutamate receptor ionotropic, NMDA 1
binder
Human
Absorption

Well absorbed orally with a bioavailability of approximately 100%. Peak plasma concentrations are reached in 3-7 hours. Food has no effect on absorption.

Volume of distribution
  • 9 to 11 L/kg
Protein binding

45%

Metabolism

Excreted largely unchanged. About 20% is metabolized to 1-amino-3-hydroxymethyl-5-methyl-adamantane and 3-amino-1-hydroxy-5,7-dimethyl-adamantane.

Route of elimination

Memantine undergoes partial hepatic metabolism. About 48% of administered drug is excreted unchanged in urine; the remainder is converted primarily to three polar metabolites which possess minimal NMDA receptor antagonistic activity: the N-glucuronide conjugate, 6-hydroxy memantine, and 1-nitroso-deaminated memantine. It is excreted predominantly in the urine, unchanged.

Half life

60-100 hours

Clearance
Not Available
Toxicity

Side effects include pain, abnormal crying, leg pain, fever, increased apetite. Adverse drug reactions include: dizziness, confusion, headache, hallucinations, tiredness. Less common side effects include: vomiting, anxiety, hypertonia, cystitis, and increased libido. Doses of up to 400 mg have been tolerated.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
16-BromoepiandrosteroneThe risk or severity of adverse effects can be increased when 16-Bromoepiandrosterone is combined with Memantine.Investigational
19-norandrostenedioneThe risk or severity of adverse effects can be increased when 19-norandrostenedione is combined with Memantine.Experimental, Illicit
5-androstenedioneThe risk or severity of adverse effects can be increased when 5-androstenedione is combined with Memantine.Experimental, Illicit
AcebutololMemantine may increase the bradycardic activities of Acebutolol.Approved
AcetazolamideAcetazolamide may decrease the excretion rate of Memantine which could result in a higher serum level.Approved, Vet Approved
AcetylcholineThe risk or severity of adverse effects can be increased when Memantine is combined with Acetylcholine.Approved
AclidiniumThe therapeutic efficacy of Aclidinium can be decreased when used in combination with Memantine.Approved
AlclometasoneThe risk or severity of adverse effects can be increased when Alclometasone is combined with Memantine.Approved
AlcuroniumThe therapeutic efficacy of Alcuronium can be decreased when used in combination with Memantine.Experimental
AldosteroneThe risk or severity of adverse effects can be increased when Aldosterone is combined with Memantine.Experimental, Investigational
AlgeldrateThe serum concentration of Memantine can be increased when it is combined with Algeldrate.Approved, Experimental
AlmagateThe serum concentration of Memantine can be increased when it is combined with Almagate.Experimental
AlmasilateThe serum concentration of Memantine can be increased when it is combined with Almasilate.Approved, Experimental
AloglutamolThe serum concentration of Memantine can be increased when it is combined with Aloglutamol.Experimental
AlprenololMemantine may increase the bradycardic activities of Alprenolol.Approved, Withdrawn
AluminiumThe serum concentration of Memantine can be increased when it is combined with Aluminium.Approved
Aluminium acetoacetateThe serum concentration of Memantine can be increased when it is combined with Aluminium acetoacetate.Experimental
Aluminium glycinateThe serum concentration of Memantine can be increased when it is combined with Aluminium glycinate.Experimental
Aluminum hydroxideThe serum concentration of Memantine can be increased when it is combined with Aluminum hydroxide.Approved
AmantadineThe risk or severity of adverse effects can be increased when Amantadine is combined with Memantine.Approved
AmcinonideThe risk or severity of adverse effects can be increased when Amcinonide is combined with Memantine.Approved
AndrostenedioneThe risk or severity of adverse effects can be increased when Androstenedione is combined with Memantine.Experimental, Illicit
AnecortaveThe risk or severity of adverse effects can be increased when Anecortave is combined with Memantine.Investigational
anecortave acetateThe risk or severity of adverse effects can be increased when anecortave acetate is combined with Memantine.Investigational
Anisotropine MethylbromideThe therapeutic efficacy of Anisotropine Methylbromide can be decreased when used in combination with Memantine.Approved
ArecolineThe risk or severity of adverse effects can be increased when Memantine is combined with Arecoline.Experimental
ArotinololMemantine may increase the bradycardic activities of Arotinolol.Approved, Investigational
ArtesunateThe serum concentration of the active metabolites of Artesunate can be reduced when Artesunate is used in combination with Memantine resulting in a loss in efficacy.Approved, Investigational
AtamestaneThe risk or severity of adverse effects can be increased when Atamestane is combined with Memantine.Investigational
AtenololMemantine may increase the bradycardic activities of Atenolol.Approved
AtracuriumThe therapeutic efficacy of Atracurium can be decreased when used in combination with Memantine.Experimental, Investigational
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be decreased when used in combination with Memantine.Approved
AtropineThe therapeutic efficacy of Atropine can be decreased when used in combination with Memantine.Approved, Vet Approved
Beclomethasone dipropionateThe risk or severity of adverse effects can be increased when Beclomethasone dipropionate is combined with Memantine.Approved, Investigational
BefunololMemantine may increase the bradycardic activities of Befunolol.Experimental
BenactyzineThe therapeutic efficacy of Benactyzine can be decreased when used in combination with Memantine.Withdrawn
BenzatropineThe therapeutic efficacy of Benzatropine can be decreased when used in combination with Memantine.Approved
BetamethasoneThe risk or severity of adverse effects can be increased when Betamethasone is combined with Memantine.Approved, Vet Approved
BetaxololMemantine may increase the bradycardic activities of Betaxolol.Approved
BethanecholThe risk or severity of adverse effects can be increased when Memantine is combined with Bethanechol.Approved
BevantololMemantine may increase the bradycardic activities of Bevantolol.Approved
BiperidenThe therapeutic efficacy of Biperiden can be decreased when used in combination with Memantine.Approved, Investigational
Bismuth SubcitrateThe serum concentration of Memantine can be increased when it is combined with Bismuth Subcitrate.Approved
Bismuth subnitrateThe serum concentration of Memantine can be increased when it is combined with Bismuth subnitrate.Experimental
BisoprololMemantine may increase the bradycardic activities of Bisoprolol.Approved
BopindololMemantine may increase the bradycardic activities of Bopindolol.Approved
BornaprineThe therapeutic efficacy of Bornaprine can be decreased when used in combination with Memantine.Experimental
BrinzolamideBrinzolamide may decrease the excretion rate of Memantine which could result in a higher serum level.Approved
BucindololMemantine may increase the bradycardic activities of Bucindolol.Investigational
BudesonideThe risk or severity of adverse effects can be increased when Budesonide is combined with Memantine.Approved
BufuralolMemantine may increase the bradycardic activities of Bufuralol.Experimental, Investigational
BupranololMemantine may increase the bradycardic activities of Bupranolol.Approved
BupropionThe serum concentration of Memantine can be increased when it is combined with Bupropion.Approved
Calcium CarbonateThe serum concentration of Memantine can be increased when it is combined with Calcium Carbonate.Approved
Calcium silicateThe serum concentration of Memantine can be increased when it is combined with Calcium silicate.Experimental
CarbacholThe risk or severity of adverse effects can be increased when Memantine is combined with Carbachol.Approved
CarteololMemantine may increase the bradycardic activities of Carteolol.Approved
CarvedilolMemantine may increase the bradycardic activities of Carvedilol.Approved, Investigational
CeliprololMemantine may increase the bradycardic activities of Celiprolol.Approved, Investigational
CevimelineThe risk or severity of adverse effects can be increased when Memantine is combined with Cevimeline.Approved
ChlorphenoxamineThe therapeutic efficacy of Chlorphenoxamine can be decreased when used in combination with Memantine.Withdrawn
CiclesonideThe risk or severity of adverse effects can be increased when Ciclesonide is combined with Memantine.Approved, Investigational
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Memantine.Approved
ClobetasolThe risk or severity of adverse effects can be increased when Clobetasol is combined with Memantine.Investigational
Clobetasol propionateThe risk or severity of adverse effects can be increased when Clobetasol propionate is combined with Memantine.Approved
ClobetasoneThe risk or severity of adverse effects can be increased when Clobetasone is combined with Memantine.Approved
ClocortoloneThe risk or severity of adverse effects can be increased when Clocortolone is combined with Memantine.Approved
CloranololMemantine may increase the bradycardic activities of Cloranolol.Experimental
Cortexolone 17α-propionateThe risk or severity of adverse effects can be increased when Cortexolone 17α-propionate is combined with Memantine.Investigational
CorticosteroneThe risk or severity of adverse effects can be increased when Corticosterone is combined with Memantine.Experimental
Cortisone acetateThe risk or severity of adverse effects can be increased when Cortisone acetate is combined with Memantine.Approved
CyclopentolateThe therapeutic efficacy of Cyclopentolate can be decreased when used in combination with Memantine.Approved
DarifenacinThe therapeutic efficacy of Darifenacin can be decreased when used in combination with Memantine.Approved, Investigational
DeflazacortThe risk or severity of adverse effects can be increased when Deflazacort is combined with Memantine.Approved
DesloratadineThe therapeutic efficacy of Desloratadine can be decreased when used in combination with Memantine.Approved, Investigational
DesonideThe risk or severity of adverse effects can be increased when Desonide is combined with Memantine.Approved, Investigational
DesoximetasoneThe risk or severity of adverse effects can be increased when Desoximetasone is combined with Memantine.Approved
Desoxycorticosterone acetateThe risk or severity of adverse effects can be increased when Desoxycorticosterone acetate is combined with Memantine.Approved
Desoxycorticosterone PivalateThe risk or severity of adverse effects can be increased when Desoxycorticosterone Pivalate is combined with Memantine.Experimental, Vet Approved
DexamethasoneThe risk or severity of adverse effects can be increased when Dexamethasone is combined with Memantine.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe risk or severity of adverse effects can be increased when Dexamethasone isonicotinate is combined with Memantine.Vet Approved
DexetimideThe therapeutic efficacy of Dexetimide can be decreased when used in combination with Memantine.Withdrawn
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Memantine.Approved
DiclofenamideDiclofenamide may decrease the excretion rate of Memantine which could result in a higher serum level.Approved
DicyclomineThe therapeutic efficacy of Dicyclomine can be decreased when used in combination with Memantine.Approved
DiflorasoneThe risk or severity of adverse effects can be increased when Diflorasone is combined with Memantine.Approved
DifluocortoloneThe risk or severity of adverse effects can be increased when Difluocortolone is combined with Memantine.Approved, Investigational
DifluprednateThe risk or severity of adverse effects can be increased when Difluprednate is combined with Memantine.Approved
DipyridamoleThe therapeutic efficacy of Memantine can be decreased when used in combination with Dipyridamole.Approved
DorzolamideDorzolamide may decrease the excretion rate of Memantine which could result in a higher serum level.Approved
EmeproniumThe therapeutic efficacy of Emepronium can be decreased when used in combination with Memantine.Experimental
EpanololMemantine may increase the bradycardic activities of Epanolol.Experimental
EpibatidineThe risk or severity of adverse effects can be increased when Memantine is combined with Epibatidine.Experimental
EquileninThe risk or severity of adverse effects can be increased when Equilenin is combined with Memantine.Experimental
EquilinThe risk or severity of adverse effects can be increased when Equilin is combined with Memantine.Approved
EsmololMemantine may increase the bradycardic activities of Esmolol.Approved
EstroneThe risk or severity of adverse effects can be increased when Estrone is combined with Memantine.Approved
Estrone sulfateThe risk or severity of adverse effects can be increased when Estrone sulfate is combined with Memantine.Approved
EtanautineThe therapeutic efficacy of Etanautine can be decreased when used in combination with Memantine.Experimental
EthopropazineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Memantine.Approved
EthoxzolamideEthoxzolamide may decrease the excretion rate of Memantine which could result in a higher serum level.Withdrawn
EtybenzatropineThe therapeutic efficacy of Etybenzatropine can be decreased when used in combination with Memantine.Experimental
FesoterodineThe therapeutic efficacy of Fesoterodine can be decreased when used in combination with Memantine.Approved
fluasteroneThe risk or severity of adverse effects can be increased when fluasterone is combined with Memantine.Investigational
FludrocortisoneThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Memantine.Approved
FlumethasoneThe risk or severity of adverse effects can be increased when Flumethasone is combined with Memantine.Approved, Vet Approved
FlunisolideThe risk or severity of adverse effects can be increased when Flunisolide is combined with Memantine.Approved, Investigational
Fluocinolone AcetonideThe risk or severity of adverse effects can be increased when Fluocinolone Acetonide is combined with Memantine.Approved, Investigational, Vet Approved
FluocinonideThe risk or severity of adverse effects can be increased when Fluocinonide is combined with Memantine.Approved, Investigational
FluocortoloneThe risk or severity of adverse effects can be increased when Fluocortolone is combined with Memantine.Approved, Withdrawn
FluorometholoneThe risk or severity of adverse effects can be increased when Fluorometholone is combined with Memantine.Approved
FluprednideneThe risk or severity of adverse effects can be increased when Fluprednidene is combined with Memantine.Approved, Withdrawn
FluprednisoloneThe risk or severity of adverse effects can be increased when Fluprednisolone is combined with Memantine.Approved
FlurandrenolideThe risk or severity of adverse effects can be increased when Flurandrenolide is combined with Memantine.Approved
Fluticasone furoateThe risk or severity of adverse effects can be increased when Fluticasone furoate is combined with Memantine.Approved
Fluticasone propionateThe risk or severity of adverse effects can be increased when Fluticasone propionate is combined with Memantine.Approved
FormestaneThe risk or severity of adverse effects can be increased when Formestane is combined with Memantine.Approved, Investigational, Withdrawn
GallamineThe therapeutic efficacy of Gallamine can be decreased when used in combination with Memantine.Experimental
Gallamine TriethiodideThe therapeutic efficacy of Gallamine Triethiodide can be decreased when used in combination with Memantine.Approved
GlycopyrroniumThe therapeutic efficacy of Glycopyrronium can be decreased when used in combination with Memantine.Approved, Investigational, Vet Approved
GTS-21The risk or severity of adverse effects can be increased when Memantine is combined with GTS-21.Investigational
HalcinonideThe risk or severity of adverse effects can be increased when Halcinonide is combined with Memantine.Approved, Investigational, Withdrawn
HE3286The risk or severity of adverse effects can be increased when HE3286 is combined with Memantine.Investigational
HexamethoniumThe therapeutic efficacy of Hexamethonium can be decreased when used in combination with Memantine.Experimental
HomatropineThe therapeutic efficacy of Homatropine can be decreased when used in combination with Memantine.Approved
HydrocortisoneThe risk or severity of adverse effects can be increased when Hydrocortisone is combined with Memantine.Approved, Vet Approved
HydrotalciteThe serum concentration of Memantine can be increased when it is combined with Hydrotalcite.Experimental, Investigational
HyoscyamineThe therapeutic efficacy of Hyoscyamine can be decreased when used in combination with Memantine.Approved
IndenololMemantine may increase the bradycardic activities of Indenolol.Withdrawn
Ipratropium bromideThe therapeutic efficacy of Ipratropium bromide can be decreased when used in combination with Memantine.Approved
IstaroximeThe risk or severity of adverse effects can be increased when Istaroxime is combined with Memantine.Investigational
KetamineThe risk or severity of adverse effects can be increased when Ketamine is combined with Memantine.Approved, Vet Approved
LabetalolMemantine may increase the bradycardic activities of Labetalol.Approved
LandiololMemantine may increase the bradycardic activities of Landiolol.Investigational
LevobunololMemantine may increase the bradycardic activities of Levobunolol.Approved
LobelineThe risk or severity of adverse effects can be increased when Memantine is combined with Lobeline.Investigational
LoteprednolThe risk or severity of adverse effects can be increased when Loteprednol is combined with Memantine.Approved
MagaldrateThe serum concentration of Memantine can be increased when it is combined with Magaldrate.Approved, Withdrawn
Magnesium HydroxideThe serum concentration of Memantine can be increased when it is combined with Magnesium Hydroxide.Approved
Magnesium oxideThe serum concentration of Memantine can be increased when it is combined with Magnesium oxide.Approved
Magnesium peroxideThe serum concentration of Memantine can be increased when it is combined with Magnesium peroxide.Experimental
Magnesium silicateThe serum concentration of Memantine can be increased when it is combined with Magnesium silicate.Approved, Experimental
Magnesium TrisilicateThe serum concentration of Memantine can be increased when it is combined with Magnesium Trisilicate.Approved
MazaticolThe therapeutic efficacy of Mazaticol can be decreased when used in combination with Memantine.Experimental
ME-609The risk or severity of adverse effects can be increased when ME-609 is combined with Memantine.Investigational
MecamylamineThe therapeutic efficacy of Mecamylamine can be decreased when used in combination with Memantine.Approved
MedrysoneThe risk or severity of adverse effects can be increased when Medrysone is combined with Memantine.Approved
MelengestrolThe risk or severity of adverse effects can be increased when Melengestrol is combined with Memantine.Vet Approved
MepindololMemantine may increase the bradycardic activities of Mepindolol.Experimental
MethacholineThe risk or severity of adverse effects can be increased when Memantine is combined with Methacholine.Approved
MethanthelineThe therapeutic efficacy of Methantheline can be decreased when used in combination with Memantine.Approved, Investigational
MethazolamideMethazolamide may decrease the excretion rate of Memantine which could result in a higher serum level.Approved
MethylprednisoloneThe risk or severity of adverse effects can be increased when Methylprednisolone is combined with Memantine.Approved, Vet Approved
Methylscopolamine bromideThe therapeutic efficacy of Methylscopolamine bromide can be decreased when used in combination with Memantine.Approved
MetipranololMemantine may increase the bradycardic activities of Metipranolol.Approved
MetixeneThe therapeutic efficacy of Metixene can be decreased when used in combination with Memantine.Approved
MetoprololMemantine may increase the bradycardic activities of Metoprolol.Approved, Investigational
MivacuriumMemantine may decrease the neuromuscular blocking activities of Mivacurium.Approved
MometasoneThe risk or severity of adverse effects can be increased when Mometasone is combined with Memantine.Approved, Vet Approved
NadololMemantine may increase the bradycardic activities of Nadolol.Approved
NCX 1022The risk or severity of adverse effects can be increased when NCX 1022 is combined with Memantine.Investigational
NebivololMemantine may increase the bradycardic activities of Nebivolol.Approved, Investigational
NicotineThe risk or severity of adverse effects can be increased when Memantine is combined with Nicotine.Approved
Oleoyl-estroneThe risk or severity of adverse effects can be increased when Oleoyl-estrone is combined with Memantine.Investigational
OrphenadrineThe therapeutic efficacy of Orphenadrine can be decreased when used in combination with Memantine.Approved
OtiloniumThe therapeutic efficacy of Otilonium can be decreased when used in combination with Memantine.Experimental, Investigational
OxitropiumThe therapeutic efficacy of Oxitropium can be decreased when used in combination with Memantine.Investigational
OxprenololMemantine may increase the bradycardic activities of Oxprenolol.Approved
OxybutyninThe therapeutic efficacy of Oxybutynin can be decreased when used in combination with Memantine.Approved, Investigational
OxyphenoniumThe therapeutic efficacy of Oxyphenonium can be decreased when used in combination with Memantine.Approved
PancuroniumThe therapeutic efficacy of Pancuronium can be decreased when used in combination with Memantine.Approved
ParamethasoneThe risk or severity of adverse effects can be increased when Paramethasone is combined with Memantine.Approved
PenbutololMemantine may increase the bradycardic activities of Penbutolol.Approved, Investigational
PentoliniumThe therapeutic efficacy of Pentolinium can be decreased when used in combination with Memantine.Approved
PhenglutarimideThe therapeutic efficacy of Phenglutarimide can be decreased when used in combination with Memantine.Experimental
PilocarpineThe risk or severity of adverse effects can be increased when Memantine is combined with Pilocarpine.Approved
PindololMemantine may increase the bradycardic activities of Pindolol.Approved
PipecuroniumThe therapeutic efficacy of Pipecuronium can be decreased when used in combination with Memantine.Approved
PirenzepineThe therapeutic efficacy of Pirenzepine can be decreased when used in combination with Memantine.Approved
Platelet Activating FactorMemantine may increase the bradycardic activities of Platelet Activating Factor.Experimental
PractololMemantine may increase the bradycardic activities of Practolol.Approved
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Memantine.Approved, Nutraceutical
Prasterone sulfateThe risk or severity of adverse effects can be increased when Prasterone sulfate is combined with Memantine.Investigational
PrednicarbateThe risk or severity of adverse effects can be increased when Prednicarbate is combined with Memantine.Approved
PrednisoloneThe risk or severity of adverse effects can be increased when Prednisolone is combined with Memantine.Approved, Vet Approved
PrednisoneThe risk or severity of adverse effects can be increased when Prednisone is combined with Memantine.Approved, Vet Approved
PregnenoloneThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Memantine.Experimental, Investigational
ProcyclidineThe therapeutic efficacy of Procyclidine can be decreased when used in combination with Memantine.Approved
PropanthelineThe therapeutic efficacy of Propantheline can be decreased when used in combination with Memantine.Approved
PropiverineThe therapeutic efficacy of Propiverine can be decreased when used in combination with Memantine.Approved, Investigational
PropranololMemantine may increase the bradycardic activities of Propranolol.Approved, Investigational
QuinidineThe therapeutic efficacy of Quinidine can be decreased when used in combination with Memantine.Approved
RapacuroniumMemantine may decrease the neuromuscular blocking activities of Rapacuronium.Withdrawn
RimexoloneThe risk or severity of adverse effects can be increased when Rimexolone is combined with Memantine.Approved
ScopolamineThe therapeutic efficacy of Scopolamine can be decreased when used in combination with Memantine.Approved
Scopolamine butylbromideThe therapeutic efficacy of Scopolamine butylbromide can be decreased when used in combination with Memantine.Approved, Vet Approved
Sodium bicarbonateThe serum concentration of Memantine can be increased when it is combined with Sodium bicarbonate.Approved
SolifenacinThe therapeutic efficacy of Solifenacin can be decreased when used in combination with Memantine.Approved
SotalolMemantine may increase the bradycardic activities of Sotalol.Approved
SuccinylcholineThe serum concentration of Succinylcholine can be increased when it is combined with Memantine.Approved
TalinololMemantine may increase the bradycardic activities of Talinolol.Investigational
TertatololMemantine may increase the bradycardic activities of Tertatolol.Experimental
TimololMemantine may increase the bradycardic activities of Timolol.Approved
TiotropiumThe therapeutic efficacy of Tiotropium can be decreased when used in combination with Memantine.Approved
TixocortolThe risk or severity of adverse effects can be increased when Tixocortol is combined with Memantine.Approved
TolterodineThe therapeutic efficacy of Tolterodine can be decreased when used in combination with Memantine.Approved, Investigational
TriamcinoloneThe risk or severity of adverse effects can be increased when Triamcinolone is combined with Memantine.Approved, Vet Approved
TrihexyphenidylThe therapeutic efficacy of Trihexyphenidyl can be decreased when used in combination with Memantine.Approved
TrimethaphanThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Memantine.Approved, Investigational
TrimethoprimThe risk or severity of adverse effects can be increased when Trimethoprim is combined with Memantine.Approved, Vet Approved
TromethamineThe serum concentration of Memantine can be increased when it is combined with Tromethamine.Approved
TropatepineThe therapeutic efficacy of Tropatepine can be decreased when used in combination with Memantine.Experimental
TropicamideThe therapeutic efficacy of Tropicamide can be decreased when used in combination with Memantine.Approved
TrospiumThe therapeutic efficacy of Trospium can be decreased when used in combination with Memantine.Approved
TubocurarineThe therapeutic efficacy of Tubocurarine can be decreased when used in combination with Memantine.Approved
UlobetasolThe risk or severity of adverse effects can be increased when Ulobetasol is combined with Memantine.Approved
UmeclidiniumThe therapeutic efficacy of Umeclidinium can be decreased when used in combination with Memantine.Approved
VareniclineThe risk or severity of adverse effects can be increased when Memantine is combined with Varenicline.Approved, Investigational
VecuroniumThe therapeutic efficacy of Vecuronium can be decreased when used in combination with Memantine.Approved
Food Interactions
  • Take without regard to meals.

References

Synthesis Reference
US3391142
General References
  1. Cacabelos R, Takeda M, Winblad B: The glutamatergic system and neurodegeneration in dementia: preventive strategies in Alzheimer's disease. Int J Geriatr Psychiatry. 1999 Jan;14(1):3-47. [PubMed:10029935]
  2. Rogawski MA, Wenk GL: The neuropharmacological basis for the use of memantine in the treatment of Alzheimer's disease. CNS Drug Rev. 2003 Fall;9(3):275-308. [PubMed:14530799]
  3. Robinson DM, Keating GM: Memantine: a review of its use in Alzheimer's disease. Drugs. 2006;66(11):1515-34. [PubMed:16906789]
  4. Rogawski MA: Low affinity channel blocking (uncompetitive) NMDA receptor antagonists as therapeutic agents--toward an understanding of their favorable tolerability. Amino Acids. 2000;19(1):133-49. [PubMed:11026482]
  5. Rammes G, Rupprecht R, Ferrari U, Zieglgansberger W, Parsons CG: The N-methyl-D-aspartate receptor channel blockers memantine, MRZ 2/579 and other amino-alkyl-cyclohexanes antagonise 5-HT(3) receptor currents in cultured HEK-293 and N1E-115 cell systems in a non-competitive manner. Neurosci Lett. 2001 Jun 22;306(1-2):81-4. [PubMed:11403963]
External Links
Human Metabolome Database
HMDB15177
KEGG Compound
C13736
PubChem Compound
4054
PubChem Substance
46506702
ChemSpider
3914
BindingDB
50062599
ChEBI
64312
ChEMBL
CHEMBL807
Therapeutic Targets Database
DAP000493
PharmGKB
PA10364
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Memantine
ATC Codes
N06DX01 — MemantineN06DA53 — Donepezil, memantine and ginkgo foliumN06DA52 — Donepezil and memantine
AHFS Codes
  • 28:92.00 — Miscellaneous Central Nervous System Agents
FDA label
Download (102 KB)
MSDS
Download (65.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingOtherAutism Spectrum Conditions/Disorders1
0RecruitingTreatmentStroke, Ischemic / Upper Extremity Weakness1
1Active Not RecruitingTreatmentBrain Cancer1
1CompletedNot AvailableHealthy Volunteers2
1CompletedNot AvailableHealthy Volunteers / Obese, Otherwise Healthy Volunteers1
1CompletedBasic ScienceBioequivalence, AUC, Cmax, Pharmacokinetics1
1CompletedBasic ScienceMajor Depressive Disorder (MDD)1
1CompletedTreatmentTobacco Use Disorders2
1Not Yet RecruitingTreatmentAlzheimer's Disease (AD)1
1RecruitingTreatmentAlzheimer's Disease (AD) / Battery1
1, 2Active Not RecruitingTreatmentChronic Orthostatic Intolerance / Tachycardia1
1, 2RecruitingHealth Services ResearchSchizophrenic Disorders1
2CompletedNot AvailableAlcohol Drinking1
2CompletedOtherAlcohol Drinking1
2CompletedSupportive CareCancer, Breast / Colorectal Cancers / Lung Cancers / Prostate Cancer / Tobacco Use Disorders1
2CompletedTreatmentAIDS-Related Dementia Complex / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAlcohol Abuse / Alcohol Dependence (Primary Condition)1
2CompletedTreatmentAmyotrophic Lateral Sclerosis (ALS)2
2CompletedTreatmentAsperger's / Asperger's Disorder / Autism Spectrum Conditions/Disorders / Autism, Early Infantile / Autistic Disorder / Pediatric Autism / Pervasive Child Development Disorder / Pervasive Developmental Disorder Not Otherwise Specified (PDD-NOS)1
2CompletedTreatmentAsperger's / Asperger's Disorder / Autism Spectrum Conditions/Disorders / Autism, Early Infantile / Autistic Disorder / Pediatric Autism / Pervasive Developmental Disorder Not Otherwise Specified (PDD-NOS)1
2CompletedTreatmentAutism Spectrum Conditions/Disorders1
2CompletedTreatmentAutism, Early Infantile1
2CompletedTreatmentAutism, Early Infantile / Pediatric Autism1
2CompletedTreatmentBipolar Disorder (BD)1
2CompletedTreatmentCocaine-Related Disorders1
2CompletedTreatmentCompulsive Buying1
2CompletedTreatmentDementia Associated With Parkinson's Disease / Diffuse Lewy Body Disease1
2CompletedTreatmentDementias1
2CompletedTreatmentHuntington's Disease (HD)1
2CompletedTreatmentKleptomania1
2CompletedTreatmentMemory Disorders / Memory, Concentration or Attention Problems / Retention Disorders, Cognitive / Subjective Cognitive Impairment1
2CompletedTreatmentObsessive-Compulsive Disorder (OCD)1
2CompletedTreatmentOpioid Dependence1
2CompletedTreatmentPain, Neuropathic1
2CompletedTreatmentPathological Gambling1
2CompletedTreatmentPendular Nystagmus Patients With Multiple Sclerosis1
2CompletedTreatmentSchizophrenic Disorders1
2Not Yet RecruitingTreatmentAmyotrophic Lateral Sclerosis (ALS) / Frontal Temporal Dementia (FTD)1
2Not Yet RecruitingTreatmentSickle Cell Disorders1
2RecruitingSupportive CareGlioma of Brain1
2RecruitingTreatmentBipolar Disorder (BD)1
2RecruitingTreatmentDisability, Intellectual / Down Syndrome (DS)1
2TerminatedTreatmentAsperger's / Asperger's Disorder / Autism Spectrum Conditions/Disorders / Autism, Early Infantile / Autistic Disorder / Pediatric Autism / Pervasive Developmental Disorder Not Otherwise Specified (PDD-NOS)1
2TerminatedTreatmentDisseminated Sclerosis1
2TerminatedTreatmentGlioblastomas1
2TerminatedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
2, 3CompletedTreatmentAlzheimer's Disease (AD) / Major Depressive Disorder (MDD) / Mild Cognitive Impairment (MCI)1
2, 3CompletedTreatmentAmyotrophic Lateral Sclerosis (ALS)1
2, 3CompletedTreatmentBipolar Disorder (BD)1
2, 3CompletedTreatmentHeroin Dependence / Opioid Dependence1
2, 3CompletedTreatmentOpioid Dependence1
2, 3Unknown StatusTreatmentCognition Disorders / Disseminated Sclerosis1
3Active Not RecruitingSupportive CareCognitive/Functional Effects / Metastatic Cancers / Neurotoxicity / Unspecified Adult Solid Tumor, Protocol Specific1
3CompletedNot AvailableAlzheimer's Disease (AD)1
3CompletedTreatmentAlzheimer's Disease (AD)5
3CompletedTreatmentAnxiety Disorders / Obsessive Compulsive Disorder (OCD)1
3CompletedTreatmentDementia of the Alzheimer's Type1
3CompletedTreatmentDepression1
3CompletedTreatmentDisseminated Sclerosis1
3CompletedTreatmentFrontotemporal Dementia1
3CompletedTreatmentGeneral Anxiety Disorder, Social Anxiety Disorder1
3CompletedTreatmentHeadache, Tension-Type1
3CompletedTreatmentOpen-angle Glaucoma (OAG)2
3CompletedTreatmentSubstance Abuse1
3Enrolling by InvitationTreatmentAOD Effects and Consequences1
3Enrolling by InvitationTreatmentBipolar Disorder II1
3Not Yet RecruitingTreatmentExcitotoxicity / Memantine / Stroke, Ischemic1
3RecruitingSupportive CareCognitive Impairments / Metastatic Malignant Neoplasm in the Brain / Solid Neoplasms1
3RecruitingTreatmentAutism Spectrum Conditions/Disorders1
3RecruitingTreatmentDepression / MCI1
3RecruitingTreatmentSchizophrenic Disorders1
3TerminatedPreventionSchizophrenic Disorders1
3TerminatedTreatmentAlzheimer's Disease (AD)2
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3TerminatedTreatmentChronic Schizophrenia1
3Unknown StatusTreatmentFibromyalgia1
4CompletedNot AvailableAlzheimer's Disease (AD)1
4CompletedBasic ScienceAlzheimer's Disease (AD)1
4CompletedTreatmentAdhd1
4CompletedTreatmentAlcoholism / Depression1
4CompletedTreatmentAlzheimer Dementia (AD)1
4CompletedTreatmentAlzheimer's Disease (AD)11
4CompletedTreatmentAphasia / Strokes1
4CompletedTreatmentAutism Spectrum Conditions/Disorders1
4CompletedTreatmentBinge Eating Disorder (BED)1
4CompletedTreatmentBipolar Disorder (BD)1
4CompletedTreatmentCRP1
4CompletedTreatmentDementia, Alzheimer Type1
4CompletedTreatmentDementias1
4CompletedTreatmentDepression1
4CompletedTreatmentDepression, Bipolar1
4CompletedTreatmentDepressive Disorders1
4CompletedTreatmentDiffuse Lewy Body Disease / Parkinson's Disease Dementia (PDD)1
4CompletedTreatmentDisseminated Sclerosis1
4CompletedTreatmentDown Syndrome (DS)1
4CompletedTreatmentFrontal Lobe Dementia / Frontotemporal Lobe Dementia / Semantic Dementia1
4CompletedTreatmentFrontotemporal Lobar Degeneration1
4CompletedTreatmentGait Disorders, Neurologic / Parkinson's Disease (PD)1
4CompletedTreatmentOculopalatal Tremor / Pendular Nystagmus1
4CompletedTreatmentOrganic Memory Impairment1
4CompletedTreatmentPTSD1
4CompletedTreatmentParkinson's Disease (PD)1
4CompletedTreatmentPhysiological Effects of Drugs1
4CompletedTreatmentSchizophrenic Disorders1
4CompletedTreatmentTremor, Essential1
4TerminatedPreventionDelirium / Post-Operative States1
4TerminatedTreatmentAlzheimer's Disease (AD)1
4TerminatedTreatmentMemory Disturbances / Mood1
4TerminatedTreatmentPain1
4TerminatedTreatmentTraumatic Brain Injury (TBI)1
4Unknown StatusTreatmentAlzheimer's Disease (AD) / Dementias1
4Unknown StatusTreatmentAphasia / Strokes1
4Unknown StatusTreatmentDementias1
4Unknown StatusTreatmentHuntington's Disease (HD)1
4Unknown StatusTreatmentModerate to Severe Alzheimer's Disease1
4Unknown StatusTreatmentPost-Operative Pain1
Not AvailableCompletedBasic ScienceHealthy Individuals1
Not AvailableCompletedBasic ScienceHealthy Volunteers1
Not AvailableCompletedTreatmentAttention Deficit Hyperactivity Disorder (ADHD) / Executive Function Deficits (EFD)1
Not AvailableCompletedTreatmentBipolar Disorder (BD)1
Not AvailableCompletedTreatmentBody Dysmorphic Disorders / Bulimia Nervosa (BN)1
Not AvailableCompletedTreatmentCognitive Impairments / Dementias / Parkinson's Disease (PD)1
Not AvailableCompletedTreatmentDementias1
Not AvailableCompletedTreatmentEpilepsies1
Not AvailableCompletedTreatmentNystagmus / Nystagmus, Pathological1
Not AvailableCompletedTreatmentObsessive-Compulsive Disorder (OCD)1
Not AvailableCompletedTreatmentParkinson's Disease (PD)1
Not AvailableCompletedTreatmentSystemic Lupus Erythematosus (SLE)1
Not AvailableCompletedTreatmentTraumatic Brain Injury (TBI)1
Not AvailableRecruitingNot AvailableSchizophrenic Disorders1
Not AvailableUnknown StatusBasic ScienceChronic Spinal Cord Injury1
Not AvailableUnknown StatusPreventionMajor Depressive Disorder (MDD)1
Not AvailableUnknown StatusTreatmentAlzheimer's Disease (AD)1
Not AvailableUnknown StatusTreatmentAsperger's Disorder / Autism, Early Infantile / Pervasive Developmental Disorder NOS1
Not AvailableUnknown StatusTreatmentDementias / Down Syndrome (DS) / Learning Disabilities1
Not AvailableUnknown StatusTreatmentFragile X Premutation Carriers / Fragile X-Associated Tremor/Ataxia Syndrome1
Not AvailableWithdrawnSupportive CareEpilepsies1
Not AvailableWithdrawnTreatmentAdhd / Executive Function Deficits (EFD's)1
Not AvailableWithdrawnTreatmentMajor Depressive Disorder (MDD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
TabletOral5 mg
Tablet, film coatedOral10 mg
Tablet, film coatedOral20 mg
SolutionOral5 mg/Pump actuation
TabletOral10 mg
Capsule, extended releaseOral
Capsule, extended releaseOral21 mg/1
Kit
LiquidOral2 mg/mL
SolutionOral2 mg/mL
TabletOral10 mg/1
TabletOral5 mg/1
Tablet, coatedOral10 mg/1
Tablet, coatedOral5 mg/1
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral5 mg/1
SolutionOral5 mg / pump actuation
KitOral
Capsule, extended releaseOral14 mg/1
Capsule, extended releaseOral28 mg/1
Capsule, extended releaseOral7 mg/1
CapsuleOral
KitOral
TabletOral5.0 mg
Prices
Unit descriptionCostUnit
Namenda 10 mg tablet3.38USD tablet
Namenda 5 mg tablet3.32USD tablet
Namenda 5-10 mg titration pk3.32USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2426492No2006-10-032023-05-08Canada
US8173708Yes2006-05-222026-05-22Us
US8283379Yes2006-05-222026-05-22Us
US8362085Yes2006-05-222026-05-22Us
US8039009Yes2009-09-242029-09-24Us
US8329752Yes2006-05-222026-05-22Us
US8598233Yes2006-05-222026-05-22Us
US8168209Yes2006-05-222026-05-22Us
US8338486No2005-11-222025-11-22Us
US8058291No2009-12-052029-12-05Us
US8580858No2005-11-222025-11-22Us
US8338485No2005-11-222025-11-22Us
US8293794No2005-11-222025-11-22Us
US5061703Yes1995-10-112015-10-11Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)258 °CPhysProp
water solubility35 mg/mL (HCl salt), 0.9 mg/mL for free baseNot Available
logP3.28HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0455 mg/mLALOGPS
logP3.31ALOGPS
logP2.07ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)10.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity54.49 m3·mol-1ChemAxon
Polarizability21.82 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9939
Blood Brain Barrier+0.9823
Caco-2 permeable+0.6082
P-glycoprotein substrateNon-substrate0.6403
P-glycoprotein inhibitor INon-inhibitor0.82
P-glycoprotein inhibitor IINon-inhibitor0.7555
Renal organic cation transporterNon-inhibitor0.7774
CYP450 2C9 substrateNon-substrate0.8213
CYP450 2D6 substrateNon-substrate0.6153
CYP450 3A4 substrateNon-substrate0.5319
CYP450 1A2 substrateNon-inhibitor0.9327
CYP450 2C9 inhibitorNon-inhibitor0.9281
CYP450 2D6 inhibitorNon-inhibitor0.872
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6795
Ames testNon AMES toxic0.6945
CarcinogenicityNon-carcinogens0.7426
BiodegradationNot ready biodegradable0.9633
Rat acute toxicity2.3455 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9839
hERG inhibition (predictor II)Non-inhibitor0.6818
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03e9-0900000000-65172d14e0f6b9102d73
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0900000000-ce475f103d528ff4d342
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0900000000-1c9199c5cf1c902223ae
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-08fr-0900000000-1bac817f714e7eec7488
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-2900000000-eb58e236084a93a3d37b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-4900000000-5a87d54400c3e9720ad0
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-052f-9500000000-95eb2b63a2392449ec4a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-9100000000-608b372857aacd60eb61
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00kf-9000000000-f283a81168372575c2aa
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0900000000-bbf1127413d0f995a000

Taxonomy

Description
This compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
Monoalkylamines
Alternative Parents
Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Organopnictogen compound / Hydrocarbon derivative / Primary aliphatic amine / Aliphatic homopolycyclic compound
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
adamantanes, primary aliphatic amine (CHEBI:64312)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Protein phosphatase 2a binding
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May ...
Gene Name
GRIN3A
Uniprot ID
Q8TCU5
Uniprot Name
Glutamate receptor ionotropic, NMDA 3A
Molecular Weight
125464.07 Da
References
  1. Smothers CT, Woodward JJ: Pharmacological characterization of glycine-activated currents in HEK 293 cells expressing N-methyl-D-aspartate NR1 and NR3 subunits. J Pharmacol Exp Ther. 2007 Aug;322(2):739-48. Epub 2007 May 14. [PubMed:17502428]
  2. Chatterton JE, Awobuluyi M, Premkumar LS, Takahashi H, Talantova M, Shin Y, Cui J, Tu S, Sevarino KA, Nakanishi N, Tong G, Lipton SA, Zhang D: Excitatory glycine receptors containing the NR3 family of NMDA receptor subunits. Nature. 2002 Feb 14;415(6873):793-8. Epub 2002 Jan 30. [PubMed:11823786]
  3. Schrattenholz A, Soskic V: NMDA receptors are not alone: dynamic regulation of NMDA receptor structure and function by neuregulins and transient cholesterol-rich membrane domains leads to disease-specific nuances of glutamate-signalling. Curr Top Med Chem. 2006;6(7):663-86. [PubMed:16719808]
  4. Foster AC, Kemp JA: Glutamate- and GABA-based CNS therapeutics. Curr Opin Pharmacol. 2006 Feb;6(1):7-17. Epub 2005 Dec 22. [PubMed:16377242]
  5. Rogawski MA, Wenk GL: The neuropharmacological basis for the use of memantine in the treatment of Alzheimer's disease. CNS Drug Rev. 2003 Fall;9(3):275-308. [PubMed:14530799]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
NMDA receptor subtype of glutamate-gated ion channels possesses high calcium permeability and voltage-dependent sensitivity to magnesium. Activation requires binding of agonist to both types of sub...
Gene Name
GRIN2A
Uniprot ID
Q12879
Uniprot Name
Glutamate receptor ionotropic, NMDA 2A
Molecular Weight
165281.215 Da
References
  1. Chen HS, Lipton SA: Pharmacological implications of two distinct mechanisms of interaction of memantine with N-methyl-D-aspartate-gated channels. J Pharmacol Exp Ther. 2005 Sep;314(3):961-71. Epub 2005 May 18. [PubMed:15901795]
  2. Maler JM, Esselmann H, Wiltfang J, Kunz N, Lewczuk P, Reulbach U, Bleich S, Ruther E, Kornhuber J: Memantine inhibits ethanol-induced NMDA receptor up-regulation in rat hippocampal neurons. Brain Res. 2005 Aug 9;1052(2):156-62. [PubMed:16009352]
  3. Bresink I, Benke TA, Collett VJ, Seal AJ, Parsons CG, Henley JM, Collingridge GL: Effects of memantine on recombinant rat NMDA receptors expressed in HEK 293 cells. Br J Pharmacol. 1996 Sep;119(2):195-204. [PubMed:8886398]
  4. Blanpied TA, Boeckman FA, Aizenman E, Johnson JW: Trapping channel block of NMDA-activated responses by amantadine and memantine. J Neurophysiol. 1997 Jan;77(1):309-23. [PubMed:9120573]
  5. Rogawski MA, Wenk GL: The neuropharmacological basis for the use of memantine in the treatment of Alzheimer's disease. CNS Drug Rev. 2003 Fall;9(3):275-308. [PubMed:14530799]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. In concert with DAPK1 at extrasynaptic site...
Gene Name
GRIN2B
Uniprot ID
Q13224
Uniprot Name
Glutamate receptor ionotropic, NMDA 2B
Molecular Weight
166365.885 Da
References
  1. Kashiwagi K, Masuko T, Nguyen CD, Kuno T, Tanaka I, Igarashi K, Williams K: Channel blockers acting at N-methyl-D-aspartate receptors: differential effects of mutations in the vestibule and ion channel pore. Mol Pharmacol. 2002 Mar;61(3):533-45. [PubMed:11854433]
  2. Nakazato E, Kato A, Watanabe S: Brain but not spinal NR2B receptor is responsible for the anti-allodynic effect of an NR2B subunit-selective antagonist CP-101,606 in a rat chronic constriction injury model. Pharmacology. 2005 Jan;73(1):8-14. Epub 2004 Sep 27. [PubMed:15452358]
  3. Maler JM, Esselmann H, Wiltfang J, Kunz N, Lewczuk P, Reulbach U, Bleich S, Ruther E, Kornhuber J: Memantine inhibits ethanol-induced NMDA receptor up-regulation in rat hippocampal neurons. Brain Res. 2005 Aug 9;1052(2):156-62. [PubMed:16009352]
  4. Blanpied TA, Boeckman FA, Aizenman E, Johnson JW: Trapping channel block of NMDA-activated responses by amantadine and memantine. J Neurophysiol. 1997 Jan;77(1):309-23. [PubMed:9120573]
  5. Rogawski MA, Wenk GL: The neuropharmacological basis for the use of memantine in the treatment of Alzheimer's disease. CNS Drug Rev. 2003 Fall;9(3):275-308. [PubMed:14530799]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Voltage-gated potassium channel activity
Specific Function
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gate...
Gene Name
HTR3A
Uniprot ID
P46098
Uniprot Name
5-hydroxytryptamine receptor 3A
Molecular Weight
55279.835 Da
References
  1. Rammes G, Rupprecht R, Ferrari U, Zieglgansberger W, Parsons CG: The N-methyl-D-aspartate receptor channel blockers memantine, MRZ 2/579 and other amino-alkyl-cyclohexanes antagonise 5-HT(3) receptor currents in cultured HEK-293 and N1E-115 cell systems in a non-competitive manner. Neurosci Lett. 2001 Jun 22;306(1-2):81-4. [PubMed:11403963]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Not Available
Specific Function
Not Available
Gene Name
CHRNA7
Uniprot ID
Q693P7
Uniprot Name
Alpha-7 nicotinic cholinergic receptor subunit
Molecular Weight
2987.635 Da
References
  1. Aracava Y, Pereira EF, Maelicke A, Albuquerque EX: Memantine blocks alpha7* nicotinic acetylcholine receptors more potently than n-methyl-D-aspartate receptors in rat hippocampal neurons. J Pharmacol Exp Ther. 2005 Mar;312(3):1195-205. Epub 2004 Nov 2. [PubMed:15522999]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Seeman P, Caruso C, Lasaga M: Memantine agonist action at dopamine D2High receptors. Synapse. 2008 Feb;62(2):149-53. [PubMed:18000814]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Voltage-gated cation channel activity
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic p...
Gene Name
GRIN1
Uniprot ID
Q05586
Uniprot Name
Glutamate receptor ionotropic, NMDA 1
Molecular Weight
105371.945 Da
References
  1. Kotermanski SE, Wood JT, Johnson JW: Memantine binding to a superficial site on NMDA receptors contributes to partial trapping. J Physiol. 2009 Oct 1;587(Pt 19):4589-604. doi: 10.1113/jphysiol.2009.176297. Epub 2009 Aug 17. [PubMed:19687120]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Busch AE, Karbach U, Miska D, Gorboulev V, Akhoundova A, Volk C, Arndt P, Ulzheimer JC, Sonders MS, Baumann C, Waldegger S, Lang F, Koepsell H: Human neurons express the polyspecific cation transporter hOCT2, which translocates monoamine neurotransmitters, amantadine, and memantine. Mol Pharmacol. 1998 Aug;54(2):342-52. [PubMed:9687576]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:34